‘You Win Again’ by Hank Williams Sr.: Heartbreaking Story Behind Timeless Tune

by Atlanta Northcutt

One of Hank Williams Sr.’s songs recorded shortly before his death carries a mournful sorrow in its lyrics and in Williams’ voice. The sadness is so effective because it comes from a painful reality.

The History Behind the Hank Williams, Sr. Hit

The truthful aching in Hank Williams’ voice is one of the reasons “You Win Again” has been covered over 100 times.

One day after the divorce from his wife Audrey became finalized, Williams Sr. recorded the hit single.


The song appeared on the backside of “Settin’ the Woods on Fire” in autumn 1952.

The track registered one week on Billboard‘s country listings sitting at No. 10 .

Hank Williams, Sr. died on New Year’s Day in 1953. This is when “You Win Again” acquired the full acknowledgment it deserved.

The song was fondly viewed from his music catalog due to the truthfulness of his lyricism. He and Audrey had a tumultuous relationship that had ended poorly upon divorce.

His sincere heartbreak written poignantly led the tune to become better-known after his passing. The song quickly began to garnish covers which have continued to be rerecorded to this day.

The Song Attracts Many Musicians

Legendary artists gave the song their own flavor, including Jerry Lee Lewis in 1957. Johnny Cash and Conway Twitty performed the song by the end of the 50s. Ray Charles and George Jones had turned the song into a multigenre tune by the mid-60s.

“You Win Again” had its sound tweaked to work for each individual performer. However, the magic continues to lie in its origin of Hank Williams, Sr.

Hank Williams, Jr. picked up the song, singing it on the soundtrack of the 1964 biopic I Remember Hank Williams.

The song has touched every genre of music, including rock ‘n roll, thanks to the Rolling Stones. Bob Dylan and the Grateful Dead have tackled it, as well. However, the only artist to take the song to the top of the charts is Charley Pride in 1980.